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Metal‐Free Deoxygenation of Carbohydrates
Author(s) -
Adduci Laura L.,
McLaughlin Matthew P.,
Bender Trandon A.,
Becker Jennifer J.,
Gagné Michel R.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201306864
Subject(s) - deoxygenation , chemistry , monosaccharide , silanes , silane , metal , organic chemistry , lewis acids and bases , cellulosic ethanol , biomass (ecology) , triol , catalysis , cellulose , oceanography , diol , geology
The conversion of readily available cellulosic biomass to valuable feedstocks and fuels is an attrative goal but a challenging transformation that requires the cleavage of multiple nonactivated CO bonds. Herein, the Lewis acid trispentafluorophenylborane (B(C 6 F 5 ) 3 ) is shown to catalyze the metal‐free hydrosilylative reduction of monosaccharides and polysaccharides to give hydrocarbons with reduced oxygen content. The choice of the silane reductant influences the degree of deoxygenation, with diethylsilane effecting the complete reduction to produce hexanes while tertiary silanes give partially deoxygenated tetraol and triol products.